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Hexane → (2S)-3-isopropoxy-N-(5-methylpyridin-2-yl)-2-(1-(3-methylpyridin-2-yl)-1H-pyrazolo[3,4-d]pyrimidin-4-yloxy)propanamide

HRID 1097996
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HRID 1097996 반응식
C[Al](C)C.CCCCCC.[CH3:11][C:12]1[CH:13]=[CH:14][C:15]([NH2:18])=[N:16][CH:17]=1.[CH:19]([O:22][CH2:23][C@H:24]([O:29][C:30]1[N:35]=[CH:34][N:33]=[C:32]2[N:36]([C:39]3[C:44]([CH3:45])=[CH:43][CH:42]=[CH:41][N:40]=3)[N:37]=[CH:38][C:31]=12)[C:25](OC)=[O:26])([CH3:21])[CH3:20]>C1(C)C=CC=CC=1>[CH:19]([O:22][CH2:23][C@H:24]([O:29][C:30]1[N:35]=[CH:34][N:33]=[C:32]2[N:36]([C:39]3[C:44]([CH3:45])=[CH:43][CH:42]=[CH:41][N:40]=3)[N:37]=[CH:38][C:31]=12)[C:25]([NH:18][C:15]1[CH:14]=[CH:13][C:12]([CH3:11])=[CH:17][N:16]=1)=[O:26])([CH3:21])[CH3:20]
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참가 물질

6

반응물 4

HCID 8058HexaneHCID 153482-Amino-5-methylpyridineHCID 16682925TrimethylaluminumHCID 59279495(2S)-Methyl 3-isopropoxy-2-(1-(3-methylpyridin-2-yl)-1H-pyrazolo[3,4-d]pyrimidin-4-yloxy)propanoate

생성물 1

HCID 57504349(2S)-3-isopropoxy-N-(5-methylpyridin-2-yl)-2-(1-(3-methylpyridin-2-yl)-1H-pyrazolo[3,4-d]pyrimidin-4-yloxy)propanamide수율 51.1%

시약·촉매·용매 1

HCID 1140Toluene용매2회

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온도
5 °C

실험 절차

A 2M solution of trimethylaluminium in hexane (0.404 mL, 0.81 mmol) was added to 5-methylpyridin-2-amine (84 mg, 0.77 mmol) in toluene (22 mL) at 5° C. under nitrogen. The resulting solution was stirred at 5° C. for 20 minutes. (2S)-Methyl 3-isopropoxy-2-(1-(3-methylpyridin-2-yl)-1H-pyrazolo[3,4-d]pyrimidin-4-yloxy)propanoate (300 mg, 0.70 mmol) (Intermediate J5) in toluene (6 mL) was added dropwise at 5° C. After the addition was complete, the solution was allowed to warm to ambient temperature and was then heated to reflux for 16 hours. The solution was allowed to cool to ambient temperature. The reaction mixture was concentrated, diluted with EtOAc (100 mL) and washed sequentially with 1M citric acid (50 mL), then saturated brine (50 mL). The organic layer was separated, dried (MgSO4) and evaporated. The residue was purified by flash silica chromatography, eluting with EtOAc to afford (2S)-3-isopropoxy-N-(5-methylpyridin-2-yl)-2-(1-(3-methylpyridin-2-yl)-1H-pyrazolo[3,4-d]pyrimidin-4-yloxy)propanamide (160 mg, 51%). 1H NMR (400 MHz, CDCl3) δ 1.09-1.12 (6H, m), 2.23 (3H, s), 2.26 (3H, s), 3.62-3.68 (1H, m), 4.00-4.09 (2H, m), 5.97 (1H, t), 7.30-7.33 (1H, m), 7.56-7.59 (1H, d), 7.70-7.73 (1H, d), 8.01-8.01 (1H, s), 8.21 (1H, d), 8.44 (1H, s), 8.46 (1H, m) 8.53 (1H, s), 9.5 (1H, broad s); m/z (ESI+) (M+H)+=448; HPLC tR=1.98 min.

후처리

  1. additionAfter the addition
  2. temperatureto warm to ambient temperature
  3. temperaturewas then heated
  4. temperatureto reflux for 16 hours
  5. temperatureto cool to ambient temperature
  6. concentrationThe reaction mixture was concentrated
  7. additiondiluted with EtOAc (100 mL)
  8. washwashed sequentially with 1M citric acid (50 mL)
  9. customThe organic layer was separated
  10. dry with materialdried (MgSO4)
  11. customevaporated
  12. customThe residue was purified by flash silica chromatography
  13. washeluting with EtOAc

출처 및 근거

ORD 기록
ord-670b6f7f85234565b841fc56631a1abd
출처 데이터셋
uspto-grants-2012_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08143263B2

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